Pyridine → HCID 67776007, compound

HRID 1408290Notes

Reaction equation

HRID 1408290 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].O1CC[CH2:16][CH2:15]1.N1C=CC=CC=1>O>[Cl:7][CH2:8][CH2:9][CH2:10][C:11]([O:6][C:1]1([CH2:15][CH3:16])[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7298CyclopentanolHCID 8028Tetrahydrofuran2×HCID 783704-Chlorobutyryl chloride

Product 1

HCID 67776007HCID 67776007, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a nitrogen atmosphere, a mixture of 69 g of 1-cyclopentyl alcohol, 118 g of 4-chlorobutyric acid chloride, and 250 g of tetrahydrofuran was ice cooled, and a mixture of 64 g of pyridine and 60 g of tetrahydrofuran was added dropwise thereto below 15° C. The reaction mixture was stirred for one day at room temperature and then ice cooled, after which 100 g of water was added dropwise to quench the reaction. This was followed by ordinary aqueous work-up and vacuum distillation (93° C./40 Pa), recovering 122 g (yield 93%) of 1-ethylcyclopentyl 4-chlorobutyrate.

Workup

  1. temperaturecooled
  2. additionwas added dropwise
  3. custombelow 15° C
  4. temperatureice cooled
  5. customto quench
  6. customthe reaction
  7. distillationThis was followed by ordinary aqueous work-up and vacuum distillation (93° C./40 Pa)

Sources & evidence

ORD record
ord-60a7b513846d4332a54c77f3bccbd57c
Source dataset
uspto-grants-2014_12
Patent number
US08921026B2

Reaction notes

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